6-bromomethyl-2-(3-bromomethyl-pyrazol-1-yl)pyridine | 526224-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-bromomethyl-2-(3-bromomethyl-pyrazol-1-yl)pyridine
• 英文别名: 2-(Bromomethyl)-6-[3-(bromomethyl)-1H-pyrazol-1-yl]pyridine；2-(bromomethyl)-6-[3-(bromomethyl)pyrazol-1-yl]pyridine
• CAS: 526224-69-1
• 化学式: C₁₀H₉Br₂N₃
• 分子量: 331.01
• InChiKey: BTKVGBCXLHDGBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromomethyl-2-(3-bromomethyl-pyrazol-1-yl)pyridine 在 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A dual lanthanide probe suitable for optical (Tb3+ luminescence) and magnetic resonance imaging (Gd3+ relaxometry)

  摘要：

  A new polyaminocarboxylate ligand derived from N, C-pyrazolylpyridine was synthesized. The luminescence and relaxometry properties of its Tb3+ and Gd3+ chelates were investigated in aqueous solutions. The Tb3+ chelate is strongly luminescent having remarkable lifetime and quantum yield (tau = 1.82 ms and Phi = 0.42). The I/T-1 proton relaxivity at 20 MHz and 25 degrees C (5.3 s(-1) mM(-1)) of the Gd3+ chelate was found to be comparable to that of the clinically used Gd-DTPA. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.091
• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 偶氮二异丁腈 、 (1S,2S)-(+)-1,2-环己二胺 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 生成 6-bromomethyl-2-(3-bromomethyl-pyrazol-1-yl)pyridine
  参考文献：
  名称：

  A dual lanthanide probe suitable for optical (Tb3+ luminescence) and magnetic resonance imaging (Gd3+ relaxometry)

  摘要：

  A new polyaminocarboxylate ligand derived from N, C-pyrazolylpyridine was synthesized. The luminescence and relaxometry properties of its Tb3+ and Gd3+ chelates were investigated in aqueous solutions. The Tb3+ chelate is strongly luminescent having remarkable lifetime and quantum yield (tau = 1.82 ms and Phi = 0.42). The I/T-1 proton relaxivity at 20 MHz and 25 degrees C (5.3 s(-1) mM(-1)) of the Gd3+ chelate was found to be comparable to that of the clinically used Gd-DTPA. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.091

文献信息

• A Water‐Stable and Strongly Luminescent Terbium(III) Macrocyclic Complex Incorporating an Intracyclic Pyrazolylpyridine Chromophore
  作者：Isabelle Nasso、Sébastien Bedel、Chantal Galaup、Claude Picard

  DOI：10.1002/ejic.200701209

  日期：2008.4

  photophysical studies were performed in aerated water on the free ligand and its GdIII complex and complexes formed with LnIII ions commonly used in fluoroimmunoassays (Ln = Sm, Eu, Tb, and Dy). The results show a wide range in the emission properties of the complexes, which can be rationalized in terms of the chromophore triplet-state energy. In particular, the TbIII complex has a remarkable overall quantum yield

  设计了一个 15 元大环配体 L1H3，目的是使水中 TbIII 离子的可见发光敏感：这种八齿螯合配体基于环内 N,C-吡唑基吡啶发色团和二亚乙基三胺三乙酸核。该配体与等摩尔量的 LnCl3 盐反应，生成具有通式 [L1·Ln(H2O)]0 的水溶性且稳定的复合物。在充气水中对游离配体及其 GdIII 复合物以及与荧光免疫分析中常用的 LnIII 离子形成的复合物（Ln = Sm、Eu、Tb 和 Dy）进行了详细的光物理研究。结果表明配合物的发射特性范围很广，这可以根据发色团三重态能量进行合理化。特别是，TbIII 复合物具有显着的总量子产率约。50 % 的 H2O（80 % 的 D2O）和从敏化剂到约 2 的铽离子的能量转移效率。85%。根据这些结果并考虑到其在水溶液中的动力学惰性，L1·Tb 复合物可被认为是一种非常有前途的候选生物亲和性分析的长寿命发光标记。(© Wiley-VCH Verlag
• Direct synthesis of new cryptates based on the N,C-pyrazolylpyridine motif
  作者：Ernesto Brunet、Olga Juanes、Miguel Angel Rodríguez-Blasco、Suzana Pereira Vila-Nueva、David Garayalde、Juan Carlos Rodríguez-Ubis

  DOI：10.1016/j.tetlet.2005.09.020

  日期：2005.11

  An expeditious synthesis of new cryptands derived from N,C-pyrazolylpyridine and their full characterization is reported. Emission lifetimes of the europium and terbium cryptates were in the range of milliseconds and terbium quantum yield was high. (c) 2005 Elsevier Ltd. All rights reserved.
• A dual lanthanide probe suitable for optical (Tb3+ luminescence) and magnetic resonance imaging (Gd3+ relaxometry)
  作者：Claude Picard、Neri Geum、Isabelle Nasso、Béatrice Mestre、Pierre Tisnès、Sophie Laurent、Robert N. Muller、Luce Vander Elst

  DOI：10.1016/j.bmcl.2006.07.091

  日期：2006.10

  A new polyaminocarboxylate ligand derived from N, C-pyrazolylpyridine was synthesized. The luminescence and relaxometry properties of its Tb3+ and Gd3+ chelates were investigated in aqueous solutions. The Tb3+ chelate is strongly luminescent having remarkable lifetime and quantum yield (tau = 1.82 ms and Phi = 0.42). The I/T-1 proton relaxivity at 20 MHz and 25 degrees C (5.3 s(-1) mM(-1)) of the Gd3+ chelate was found to be comparable to that of the clinically used Gd-DTPA. (c) 2006 Elsevier Ltd. All rights reserved.